2) Man who seduces young virgins.
2) "You're dating another Freshman English major? You are such a cherry picker!"
A common example comes from basketball, in which a "cherry picker" is a person who favors short shots, but especially a person who sits in the back court by the basket waiting for an outlet pass on a change of possession, enabling them to score easily before any defenders can reach them.
The origins of this term may come from the notion of "cherry picking" as attempting, or picking, only those things that are easily obtained, or only what suits your taste best, as a cherry might.
So when they say that they need a cherry picker, they mean they need an Engine Hoist. These hoists lift out the engines and transmissions (and transaxles) from cars and trucks.
"Ok, let me wheel that sucker over there. Hold on."